WO2000005961A1 - Agents antibacteriens et antimoisissures pour fibres, procede de traitement associe et produits fibreux ainsi traites - Google Patents

Agents antibacteriens et antimoisissures pour fibres, procede de traitement associe et produits fibreux ainsi traites Download PDF

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Publication number
WO2000005961A1
WO2000005961A1 PCT/JP1999/004020 JP9904020W WO0005961A1 WO 2000005961 A1 WO2000005961 A1 WO 2000005961A1 JP 9904020 W JP9904020 W JP 9904020W WO 0005961 A1 WO0005961 A1 WO 0005961A1
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WO
WIPO (PCT)
Prior art keywords
antibacterial
antifungal
mildewproofing
antifungal agent
fibers
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP1999/004020
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English (en)
Japanese (ja)
Inventor
Kenichi Miyamoto
Itsumi Nakamura
Masahiro Makino
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nicca Chemical Co Ltd
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Nicca Chemical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nicca Chemical Co Ltd filed Critical Nicca Chemical Co Ltd
Publication of WO2000005961A1 publication Critical patent/WO2000005961A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • A01N55/02—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing metal atoms

Definitions

  • Antimicrobial and antifungal agent for textiles antimicrobial and antifungal processing method and antimicrobial and antifungal fiber products
  • the present invention relates to an antibacterial and antifungal agent for fibers, an antibacterial and antifungal processing method, and an antibacterial and antifungal fiber product.
  • antibacterial agents include quaternary ammonium salt compounds (JP-A-3-38552, JP-B-1333589, etc.), and silver-based compounds (JP-A-6-182) Japanese Patent Application Laid-Open Nos. 2419392/92, J-type organic compounds (Japanese Patent Application Laid-Open No. 6-192962), Chlorine-based organic compounds (Japanese Patent Application Laid-Open No. Hei 1-266627), etc.
  • quaternary ammonium salt compound or a chlorine-based organic compound is used in combination with thiabendazole as an antibacterial agent as an antibacterial agent, but these also discolor due to heat and affect the environment due to chlorine. And the lack of durability for washing. Disclosure of the invention
  • the present invention provides various antibacterial and antifungal agents, such as having a narrow antibacterial vector, a limited processing method, causing discoloration, and lacking durability to washing.
  • Providing an antibacterial and antifungal agent for textiles that solves the problem and enables antibacterial and antifungal processing of textile products by post-processing, an antibacterial and antifungal processing method, and a textile product that has been subjected to antibacterial and antifungal processing This was done for this purpose.
  • the inventors of the present invention have conducted intensive studies on the above problems, and as a result, have found that a finely divided metal salt of bis (1-hydroxy2 (1H) pyridinthionone 0, S) 1-1 (T-14) is used as a fiber. It has been found that the above problem can be solved by using it as an antibacterial and antifungal agent for use, and the present invention has been completed based on this finding.
  • the present invention relates to an aqueous dispersion of 1 to 60% by weight of a metal salt of finely divided bis (1-hydroxy-2- (1H) pyridinionate 1 ⁇ , S) — (T-4).
  • the present invention provides an antibacterial and antifungal agent for fibers, a method for processing a fiber product using the antibacterial and antifungal agent, and an antibacterial and antifungal fiber product.
  • the metal salt of bis (1-hydroxy-2 (1H) pyridinone protein 0, S)-(T-4) used as an antibacterial and antifungal agent component is zinc salt or Copper salts are preferred.
  • the antibacterial and antifungal agent for fibers according to the present invention preferably comprises bis (1—hydroxy-2 (1H) pyridinoneone 0, S) — (T) as an antibacterial and antifungal agent component.
  • the metal salt of 1) contains zinc oxide.
  • a metal salt of bis (1-hydroxy-2 (1H) pyridinionate—0, S)-(T-14) is preferably 1 to 60% by weight of the antibacterial antifungal agent. Or 1 to 30% by weight.
  • a metal salt of bis (1—hydroxy-2 (1H) pyridinionate-10, S) — (T-14) is contained in the antibacterial antifungal agent.
  • zinc oxide contains about 60% by weight, more preferably 1 to 30% by weight.
  • the cumulative volume distribution of the particle diameter is 50% or less, and the particle diameter is 1 zm or less. More preferably, 80% of the cumulative volume distribution has a particle size of 3 m or less, and particularly preferably, 95% of the cumulative volume distribution of the particle size has a particle size of 5 am or less.
  • the interface ratio is preferably 0.1 to 50% by weight, more preferably 1 to 50% by weight, based on the antibacterial and antifungal agent components.
  • the activator it is possible to obtain a stable aqueous dispersion which is finely divided in a suitable state.
  • a non-ionic surfactant such as polyoxyalkylene alkyl ether, polyoxyalkylene alkyl amine polyoxyalkylene styrenated polyester, or the like, is preferable.
  • this nonionic surfactant has an HLB of 15 or more
  • Anionic surfactants such as xyalkylene alkyl ether sulfonate, polyoxyalkylene styrenated phenyl ether sulfonate and polycyclic heterocyclic sulfonate are exemplified.
  • the micronization can be performed by using a micronization machine such as a sand grinder after the above-mentioned antibacterial and antifungal agent component, surfactant and water are pre-dispersed with a stirrer.
  • the antibacterial and antifungal agent of the present invention is micronized by the above-described method, whereby the antibacterial and antifungal property of textile products is improved in washing resistance, and the conventional antibacterial and antifungal agent is used.
  • the sedimentation of the bicomponent component is eliminated, and even if settled, solidification as in the past does not occur and redispersion and restoration can be easily performed.
  • the micronization according to the present invention allows the powdering phenomenon due to physical impact at the treatment site, which is a problem with the conventional powder dispersion, and poor compatibility with agents such as softeners and fluorescent dyes.
  • Various problems such as the occurrence of scum due to noise can be improved.
  • the textile products to be processed in the present invention include synthetic fibers such as polyester, nylon, and acryl, natural fibers such as cotton, hemp, and wool, and composite fibers of synthetic fibers and natural fibers.
  • synthetic fibers such as polyester, nylon, and acryl
  • natural fibers such as cotton, hemp, and wool
  • composite fibers of synthetic fibers and natural fibers include various fiber products such as yarn, fabric, knitted fabric and nonwoven fabric. In particular, it is preferable because there is no problem such as discoloration when used for a white textile product.
  • the antibacterial and antifungal agent of the present invention has a stable dispersion state obtained by fine-graining when processed into textile products, and is subjected to all processes such as padding treatment, immersion treatment, dye bath and bath treatment, and coating. It can be used without restriction in the processing process.
  • Textile products processed with the antibacterial and antifungal agent of the present invention exhibit durability to washing under ordinary household washing conditions, even if they are not processed in combination with a binder resin.
  • the binder resin used at this time is, for example, N-methylol, glyoxal, urethane, polyester, acryl, epoxy or polyvinyl alcohol.
  • Example 2 Except that the nonionic surfactant XTD-15 was replaced by Anionic surfactant 5SP-10S (polyoxyethylene styrenated polyphenylene sulfonate ammonium salt manufactured by Nika Chemical Co., Ltd.) In the same manner as in Example 1, the cumulative volume distribution of the particle diameter 50% particle diameter 0.5 / m, An antibacterial and antifungal agent for fibers was obtained, which had a particle diameter of 0.7% and a particle diameter of 0.7 m with a cumulative particle size distribution of 80% and a particle diameter of 1.9 with a particle diameter of 1.9.
  • 5SP-10S polyoxyethylene styrenated polyphenylene sulfonate ammonium salt manufactured by Nika Chemical Co., Ltd.
  • Sandglai Dispersion treatment for 4 hours by a duster cumulative volume distribution of particle size 50% particle size 0.5 m, particle size cumulative volume distribution 80% particle size 0.9 // m, particle size integration
  • An antibacterial and antifungal agent for fibers with a volume distribution of 95% and a particle size of 2.1 / m was obtained.
  • Example 5 The mixture having the same composition as in Example 3 was pre-dispersed with a stirrer, and then subjected to a dispersion treatment for 1 hour with a sand grinder manufactured by Igarashi Kikai Seisakusho Co., Ltd. to obtain a cumulative particle size distribution of 50% and a particle size of 1.2%. m, particle size cumulative volume distribution 80% particle size 2.8m, particle size cumulative volume distribution 95% particle size 4.9m Was.
  • Example 5 Example 5
  • Example 1 70 parts by weight of the micronized antibacterial antifungal agent obtained in Example 1 and the mixture having the same composition as in Example 1 were preliminarily dispersed with a stirrer, and the particle diameters obtained without performing the micronized dispersion treatment were integrated.
  • the mixture was mixed with 30 parts by weight of a fungicide to obtain an antibacterial and antifungal agent for fibers.
  • the particle size of this antibacterial and antifungal agent for fibers is as follows.
  • the cumulative volume distribution of the particle diameter was 2.8 / Xm with a particle size of 80%, and the cumulative volume distribution of the particle diameter was 5.2 / m with a 95% volume distribution.
  • the mixture having the same composition as in Example 1 was only preliminarily dispersed with a stirrer without performing fine particle dispersion treatment, and the cumulative volume distribution of the particle diameter was 50%, the particle diameter was 2.2 m, and the cumulative volume distribution of the particle diameter was 8 An antibacterial and antifungal agent for fibers having a particle diameter of 6.3 m and a cumulative particle size distribution of 95% and a particle diameter of 9.0 m was obtained.
  • the antibacterial and antifungal agents for fibers of Examples 1 to 5 and Comparative Example 1 were evaluated for static stability, mechanical impact stability, and compatibility with other drugs.
  • Table 1 shows that the antimicrobial antifungal agent for fibers finely divided according to the present invention has excellent stability.
  • a 10% by weight aqueous solution of benzalkonium chloride was prepared.
  • polyester cloth, cotton cloth, polyester-cotton blended cloth, nylon cloth, acryl knit, wool cloth, and polyester knit were used. After treatment, antibacterial properties, antifungal properties and whiteness were evaluated.
  • the processing sample was a polyester Z cotton blended cloth (mixture ratio 65 Z3
  • Polyesternit was used as the sample to be treated, and the dye CI Disperse Red 167 was added with l% o.w.f. and a dispersant RM-EX (manufactured by Nika Chemical Co., Ltd.). 5 g / liter and 90% industrial acetic acid 0.3 g Z liter with antibacterial antifungal agent and water in the amount shown in Table 7 in a bath consisting of 30 g at 130 ° C 1 minute Z-Little, 1 g Z-Little, Soda-ash 1 g Z-Little Knob and Sorbet Sunmol RC-700 (Nichika Chemical Co., Ltd.) ) A soaking treatment bath having a composition of 1 g / liter was subjected to a soaking treatment at 80 ° C for 20 minutes, washed with water and dried, and subjected to an evaluation test. The obtained results are shown in Table 7 (Examples 51 to 54, Comparative Examples 18 to 19).
  • the washing method performed at the time of the evaluation test is as follows.
  • Washing method 1 washing method for general household
  • Laundry method 2 Laundry method for industrial use
  • Washing method 3 Dry cleaning method
  • Antibacterial properties, antifungal properties and whiteness were evaluated as follows.
  • the test was conducted in accordance with the method described in the manual for the quantitative antibacterial test method for textile products issued by the Textile Product New Function Evaluation Council (unified test method).
  • Staphylococcus aureus StaphylococecusaruseusIF013732
  • Klebsiella pneumoniae Klebsiella pneumoniae
  • ⁇ The number of viable bacteria on the sample after 18 hours is less than the initial number of bacteria for two species.
  • ⁇ The number of viable bacteria on the sample after 18 hours and the initial number of cultured bacteria are similar for the two bacteria.
  • the number of viable bacteria on the sample after 18 hours is greater than the initial number of bacteria.
  • the measurement was performed according to the method of JIS Z 2911.
  • Aspergillus niger AsspergirlunisnigerIF06341) and Kahi (Penicc11) iumcitrinumIFO6352) were used.
  • + + + The growth of vitreous with a sample area of 1 Z 3 or more and less than 2 Z 3 is observed on the sample.
  • + + + Mold growth of 2/3 or more of the sample area was observed on the sample
  • Treatment bath composition (% by weight)
  • Treatment bath composition (% by weight)
  • Treatment bath composition (% by weight)
  • an antibacterial and antifungal agent for textiles which is a finely divided, stable aqueous dispersion. It is possible to obtain an antibacterial and antifungal processed fiber product which has no problem such as yellowing and is durable to washing.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

L'invention concerne des agents antibactériens et antimoisissures pour fibres, qui contiennent 1 à 60 % en poids d'un sel métallique corpusculé de (1-hydroxy-2-1H)pyridinethionate(O,S)-(T-4) en dispersion aqueuse; un procédé de traitement antibactérien et antimoisissures, qui consiste à traiter des produits fibreux avec les agents ci-dessus; ainsi que les produits fibreux antibactériens et antimoisissures traités par lesdits agents.
PCT/JP1999/004020 1998-07-28 1999-07-27 Agents antibacteriens et antimoisissures pour fibres, procede de traitement associe et produits fibreux ainsi traites Ceased WO2000005961A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP10/213124 1998-07-28
JP21312498 1998-07-28

Publications (1)

Publication Number Publication Date
WO2000005961A1 true WO2000005961A1 (fr) 2000-02-10

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PCT/JP1999/004020 Ceased WO2000005961A1 (fr) 1998-07-28 1999-07-27 Agents antibacteriens et antimoisissures pour fibres, procede de traitement associe et produits fibreux ainsi traites

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001288017A (ja) * 2000-04-04 2001-10-16 Osaka Kasei Kk 抗菌・抗カビ加工用ピリチオン亜鉛含有分散液及び該分散液を用いた繊維類の抗菌・抗カビ加工方法
JP2007107144A (ja) * 2005-10-14 2007-04-26 Chisso Corp 親水性を有する抗菌・消臭性繊維、繊維成形品及び繊維製品
CN111868323A (zh) * 2018-03-30 2020-10-30 大阪化成株式会社 抗菌防霉性纤维结构物

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3785985A (en) * 1971-04-21 1974-01-15 Colgate Palmolive Co Cosmetic and textile-treating compositions
JPS4919029A (fr) * 1972-03-27 1974-02-20
JPS5292881A (en) * 1976-01-30 1977-08-04 Nonogawa Shoji Yk Method of manufacturing aqueous suspension
JPS60139613A (ja) * 1983-12-27 1985-07-24 Kao Corp 抗菌剤分散液および抗菌性毛髪処理剤組成物
JPS6157503A (ja) * 1984-08-29 1986-03-24 Kao Corp 抗菌剤懸濁液および抗菌性毛髪処理剤組成物
JPS6263A (ja) * 1985-03-28 1987-01-06 Kao Corp ２−メルカプトピリジン−ｎ−オキシド多価金属塩微粒子の製造方法
JPH0820733A (ja) * 1994-07-07 1996-01-23 Kansai Paint Co Ltd 塗料用抗菌剤分散液
JPH0853313A (ja) * 1994-08-11 1996-02-27 Kanae Toryo Kk 水中防汚剤
JPH09157112A (ja) * 1995-12-06 1997-06-17 Toyobo Co Ltd 生物抵抗性を有する樹脂複合繊維シート

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3785985A (en) * 1971-04-21 1974-01-15 Colgate Palmolive Co Cosmetic and textile-treating compositions
JPS4919029A (fr) * 1972-03-27 1974-02-20
JPS5292881A (en) * 1976-01-30 1977-08-04 Nonogawa Shoji Yk Method of manufacturing aqueous suspension
JPS60139613A (ja) * 1983-12-27 1985-07-24 Kao Corp 抗菌剤分散液および抗菌性毛髪処理剤組成物
JPS6157503A (ja) * 1984-08-29 1986-03-24 Kao Corp 抗菌剤懸濁液および抗菌性毛髪処理剤組成物
JPS6263A (ja) * 1985-03-28 1987-01-06 Kao Corp ２−メルカプトピリジン−ｎ−オキシド多価金属塩微粒子の製造方法
JPH0820733A (ja) * 1994-07-07 1996-01-23 Kansai Paint Co Ltd 塗料用抗菌剤分散液
JPH0853313A (ja) * 1994-08-11 1996-02-27 Kanae Toryo Kk 水中防汚剤
JPH09157112A (ja) * 1995-12-06 1997-06-17 Toyobo Co Ltd 生物抵抗性を有する樹脂複合繊維シート

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001288017A (ja) * 2000-04-04 2001-10-16 Osaka Kasei Kk 抗菌・抗カビ加工用ピリチオン亜鉛含有分散液及び該分散液を用いた繊維類の抗菌・抗カビ加工方法
JP2007107144A (ja) * 2005-10-14 2007-04-26 Chisso Corp 親水性を有する抗菌・消臭性繊維、繊維成形品及び繊維製品
CN111868323A (zh) * 2018-03-30 2020-10-30 大阪化成株式会社 抗菌防霉性纤维结构物
CN111868323B (zh) * 2018-03-30 2023-03-21 大阪化成株式会社 抗菌防霉性纤维结构物

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